Chirality & Odour Perception
John C. Leffingwell, Ph.D.

The 5-Methyl-norlimbanols

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Photo by permission of M. Roudintska - Art & Parfum

(1'R,6'S)-(+)-5-methyl-norlimbanol - woody, resembles (+)-1'R,3S,6'S-norlimbanol (strong very elegant woody-amber note) (Schulte-Elte, et al.); also described as highly diffusible, sharp amber fragrance with slight camphorous side note (Ohmoto et al. for a 95.2: 4.8 % ratio of trans/cis isomers)

= (+)-(1'R,6'S)-5-methyl-1-(2',2',6'-trimethyl-1'-cyclohexyl)-3-hexanol

Note that the C-3 position is epimeric, so this actually is a mixture of (1'R,3S,6'S) & (1'R,3R,6'S) isomers

Ref: Schulte-Elte, et al., Optically active aliphatic alcohols and their use as perfuming ingredients, United States Patent 6,054,426, April 25, 2000, assigned to Firmenich; Ohmoto, Tatsuya; Shimada, Akemi; Yamamoto, Takeshi; Propanol derivatives and perfumes containing the same, United States Patent RE37,159 May 1, 2001 & United States Patent 5,250,512, Oct. 5, 1993, Assigned to Takasago International Corp.

(1'S,6'R)-(-)-5-methyl-norlimbanol - very weak and devoid of animal character (Schulte-Elte, et al.); also described as a faint woody odor with a little moldiness (Ohmoto et al. for a 95.1: 4.9 % ratio of trans/cis isomers)

= (-)-(1'S,6'R)-5-methyl-1-(2',2',6'-trimethyl-1'-cyclohexyl)-3-hexanol

Note that the C-3 position is epimeric, so this actually is a mixture of (1'S,3R,6'R) & (1'S,3S,6'R) isomers

Ref: Schulte-Elte, et al., Optically active aliphatic alcohols and their use as perfuming ingredients, United States Patent 6,054,426, April 25, 2000, assigned to Firmenich; Ohmoto, Tatsuya; Shimada, Akemi; Yamamoto, Takeshi; Propanol derivatives and perfumes containing the same, United States Patent RE37,159 May 1, 2001 & United States Patent 5,250,512, Oct. 5, 1993, Assigned to Takasago International Corp.

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

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Copyright 2001 - Leffingwell & Associates